Built in the field and designed to scale.

Cold start. No enterprise infrastructure. Twelve months later, a team closing seven figure Fortune 100 deals.

I inherited Twilio’s North America new business team selling into the Fortune 1000: 30+ product led reps, no hunting motion, no qualification discipline, and no forecast the team could trust.

In twelve months, I rebuilt the AE and Director bench, verticalized the teams, moved sellers into the field with customers and partners, and installed the operating discipline required to move upmarket. That included implementation of the Challenger Sales methodology, six hard gates, AE self certification and manager sign off, a deal control playbook, the weekly cross functional Deal Walk, a new compensation plan, and a coaching cadence that reinforced the standards.

• 126% of plan, $40M+ ARR contracted
• 5.5× pipeline generation against target
• 25% → 70%+ enterprise revenue mix in twelve months
• Under 50% → just above 70% opportunity forecast accuracy, measured at day 45 of the quarter

A SaaS platform geared to SMB with no enterprise motion. 18 months later, winning Fortune 250 logos. Then an $850M exit.

Zipwhip sold to small business. I was brought in to move the company upmarket, I defined the enterprise ICP against real board skepticism, and build the motion from the field up. We started in a regulated industry, insurance. The team got on site with customers, inside their call centers, close enough to see and understand the operating pain and compliance requirements before we built the playbook. Retail and Financial Services followed. The platform had to grow with the motion, so I partnered closely with Product and Engineering to harden the enterprise feature set (RBAC, SSO, analytics, hierarchical account design) while project managing the implementation of SOC 2 Type II across the company.

The Guidewire alliance opened P&C insurance; Salesforce AppExchange opened the rest. The ecosystem started to compound as partners carried us into accounts we would never have reached cold.

The harder lesson was internal. Owning the full customer facing surface meant the coalition work landed on me: pricing, billing, support, product, marketing, and legal all had to harden around deals none of them had been built for. Big deals create downstream effects you do not anticipate until you have broken glass. Those breaks are what taught me to build a revenue operating model that is resilient to internal fragility rather than dependent on nothing going wrong.

Twilio acquired Zipwhip for $850M.

• Farmers: multi million dollar expansion
• Goldman Sachs–led Series D
• Guidewire alliance
• Salesforce AppExchange
• SOC 2 Type II

Employee #26. No B2B function. No enterprise motion. Twelve months later: a Tier 1 customer base.

Glympse was a true zero to one enterprise build: a consumer location sharing app with no B2B function, no ICP, no sales motion, no pipeline, and no reference customer. I had used the product religiously, saw the enterprise opportunity in last mile customer experience before there was a motion around it, and sought out the company to help create the market.

As employee #26 and the first B2B sales leader, I proved product market fit across field service automation, last mile logistics, and customer experience by multithreading across Field Operations and Technology, riding in service vehicles, sitting in call centers, identifying the value impact, and leading the executive briefing with the CIO and SVP of Field Operations. That work led to the Time Warner/Charter deal within twelve months of first touch.

That one deal (17,000 field technicians) defined the ICP and everything that followed. Rogers closed inside the same twelve months. TruGreen and Papa John’s came off the same pattern, built from a standing start against companies a hundred times our size.

• Charter: 17,000 field technicians
• Rogers
• TruGreen
• Papa John’s

Three builds inside one company: make the market, run it at scale, then learn the other side of the table.

2000–2006 · Make the market

There was no wireless data market. Enterprise wireless data started inside a joint venture between AT&T Wireless and NTT DoCoMo, staffed largely from enterprise software and management consulting, with real operating rigor from day one. We had to make the market: quantify before and after value, identify the industries with the clearest need and lowest barriers to entry, build the solution partner ecosystem, and design a multithreaded sales motion across Line of Business and IT. The business grew from nearly $0 to a $300M+ ARR book over six years, selling early workforce automation into the Fortune 500. I was the top RVP in the country five years out of six.

The durable piece was enablement, and it was mine end to end. Not a methodology bought off a shelf. I wrote the content, designed the approach, built the grading methodology, and structured it in three levels. At the center was a live panel role play where AEs and Directors sold to a CIO, line of business VP, IT manager, and procurement, each armed with questions written in advance. Sellers were graded 360 degrees. Hard, but built for growth, not failure. Level 3 earned a seat in a vertical industry Center of Excellence with their top deals, turning training into operating leverage.

AT&T Mobility’s Learning Services organization later called it the best training program they had seen. 225+ AEs and Sales Directors went through it. At the annual kickoff, I received the Innovation Award for work credited with helping take the organization past $1B in ARR. DHL came out of this period too: 26,000 vehicles, a custom proof of delivery solution, and months riding with drivers and sitting with dispatchers before anyone wrote a requirement.

2007–2008 · Run it at scale

Then the Signature branch on the West Coast: Fortune 300 accounts, a $500M book of business, full P&L, and every customer facing role, including revenue operations. It became the number one sales branch in the nation. In the same window, I ran two companywide top ten mega deals simultaneously: Boeing at $100M ARR and Microsoft at $50M ARR.

Boeing was a competitive takeout of more than 65,000 devices against Verizon, Sprint, and T-Mobile, moving from under 18% share to effectively all of it. It took 23 internal business cases, custom SLAs, a first of its kind fixed mobile convergence plan, dedicated billing and support, in building antenna systems across 200 campuses, and a negotiated first right of refusal on any telecom service Boeing bought for the life of the deal. The contract was signed at $500M over five years and billed more than $700M.

2009–2015 · The other side of the table

Then I made a deliberate shift out of enterprise sales to help build a new division inside AT&T Mobility around mobile computing. I ran business development and product marketing: exclusive device and platform deals with Microsoft, Google, Amazon, and Samsung; the silicon and ODM relationships behind them across Asia; and go to market across AT&T Mobility’s consumer and business channels.

That chapter gave me depth enterprise selling alone never would have. Negotiating alongside AT&T Mobility’s supply chain, I sat on the buy side of nine figure technology deals and saw how vendors built their cases, where they earned trust, and where they lost it. Most people advising on enterprise go to market have only ever been on one side of that table.

• Boeing: $100M ARR, $500M signed, $700M+ billed
• Microsoft: $50M ARR, closed in the same window
• DHL: 26,000-vehicle deployment
• Exclusive OEM deals: Microsoft, Google, Amazon, Samsung
• Sales certification program I authored: 3 levels, 225+ enterprise sellers
• Innovation Award: credited with enabling the org past $1B